Compositions containing beta substituted acrylic acid amides as preservatives

ABSTRACT

Compounds having the formula:   &lt;IMAGE&gt;   wherein R1 is alkyl or alkenyl containing 1 to 20 carbon atoms, X is S, SO or SO2, and R2 and R3, which can be the same or different, are hydrogen, alkyl containing 1 to 20 carbon atoms, oxyalkylene containing 1 to 20 units of ethylene oxide or propylene oxide, 2-sulfoethyl or a salt thereof, or 2-carboxyethyl or a salt thereof, are incorporated, as a preservative or anti-microbial agent in compositions that are subject to deterioration by the action of micro-organisms, excluding foods and medicines.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is related to U.S. Ser. No. 699,324, filed June 24,1976, now abandoned and replaced by Ser. No. 807,509, and U.S. Ser. No.702,405, filed July 6, 1976, now abandoned and replaced by Ser. No.818,951, the entire contents of which are incorporated herein byreference.

The present invention relates to non-pharmaceutical compositions whichare subject to deterioration by the action of micro-organisms and whichcontain as a preservative, one or a mixture of compounds having theformula (I): ##STR2## wherein R₁ is alkyl or alkenyl containing 1 to 20carbon atoms, X is S, SO or SO₂, and R₂ and R₃, which can be the same ordifferent, are hydrogen, alkyl containing 1 to 20 carbon atoms,oxyalkylene containing 1 to 20 units of ethylene oxide or propyleneoxide, 2-sulfoethyl or a salt thereof, or 2-carboxyethyl or a saltthereof.

The present inventors have often utilized different conventionalantimicrobial agents as germicides, fungicides or antiseptics, butvarious problems have been encountered in their use. The differentconventional antimicrobial agents were developed for the initial purposeof obtaining antimicrobial activity, but those that were supposed tohave an extensive scope of usefulness at the time of their initialdevelopment often proved to be unsatisfactory as applied to new systemsor compositions.

In order to overcome the microbial deterioration of cosmetics andhousekeeping sundries, for example, it is conventional to measure firstthe degree of antimicrobial activity independently from thephysico-chemical features of the system, for example, by admixingantimicrobial agents such as benzoic acid, and aromatic phenol compoundsfor example salicylic acid or alkali salts thereof, p-hydroxybenzoicacid esters, p-isopropyl-o-methylphenol or o-phenylphenol, or by addingthe so-called invert soaps such as alkylbenzyldimethylammonium halides,and then examine their compatibility and stability in the mentionedsystems for a long time period. However, these examinations requirelong-term testing of numerous chemicals for many test items. It isgenerally found that very few chemicals are satisfactory for aparticular purpose. Furthermore, different systems of chemicals requirethe same test processes so that many tests must be carried outrepeatedly and many man-hours are required to do the testing. Thispresents serious difficulties to the plan of developing the market forthese compositions. In addition, because the conventional antimicrobialchemicals mentioned above have been utilized for a long period and inwide ranges of amounts, many resistant microorganisms have appeared andprevention of microbial contamination, for example, in productionplants, is very difficult.

Therefore, it is desired to provide more chemicals having an excellentand wide-ranging antimicrobial activity for use in various compositions.

We have found that the formula (I) compounds have both physicochemicalproperties and antimicrobial activity that make them highly effectivefor use as preservatives in various compositions, such as cosmetics.

The formula (I) compounds include the following typical examples:

1. β-alkylsulfenyl-acrylic acid amides, for example, n--C₈ H₁₇--S--CH═CH--CONH₂ (n_(D) ²⁰ =1.5168)

2. β-alkylsulfinyl-acrylic acid amides, for example, ##STR3## 3.β-alkylsulfonyl-acrylic acid amides, for example, ##STR4## 4.β-alkylsulfenylacrylic acid dialkylamides, for example, ##STR5## 5.β-alkylsulfinyl-acrylic acid dialkylamides, for example, ##STR6## 6.β-alkylsulfonyl-acrylic acid dialkylamides, for example, ##STR7## 7.β-alkylsulfenyl-acrylic acid di-(2-hydroxyethyl)-amides, for example,n--C₈ H₁₇ --S--CH═CH--CON(CH₂ CH₂ OH)₂ (n_(D) ²⁰ =1.5272)

8. β-alkylsulfinyl-acrylic acid di(2-hydroxyethyl)-amides, for example,##STR8## 9. β-alkylsulfonyl-acrylic acid di-(2-hydroxyethyl)-amides, forexample, ##STR9## 10. β-alkylsulfenyl-acrylic acid 2-sulfoethylamides,for example, n--C₈ H₁₇ --S--CH═CH--CONHCH₂ CH₂ SO₃ Na (M.P. 86°-87° C.)

11. β-alkylsulfinyl acrylic acid 2-sulfoethyl amides, for example,##STR10## 12. β-alkylsulfonyl-acrylic acid 2-sulfoethylamides, forexample, ##STR11## 13. β-alkylsulfenyl-acrylic acid2-carboxyethylamides, for example, n--C₈ H₁₇ --S--CH═CH--CONHCH₂ CH₂COONa (M.P. 57°-58° C.)

14. β-alkylsulfinyl-acrylic acid 2-carboxyethylamides, for example,##STR12## 15. β-alkylsulfonyl-acrylic acid 2-carboxyethylamides, forexample, ##STR13##

The formula (I) compounds of the invention are prepared as follows:

A mercaptan having the formula:

    R.sub.1 -SH                                                (II)

wherein R₁ has the same meaning as defined above, is reacted withacetylene-monocarboxylic acid, in an aqueous solution of an alkali metalhydroxide, to form β-sulfenylacrylic acid having the formula:

    R.sub.1 --S--CH═CH--COOM                               (III)

wherein M is hydrogen or alkali metal, and R₁ has the same meaning asdefined above. Then the obtained β-sulfenylacrylic acid (III), or theβ-sulfenylacrylic acid halide obtainable by halogenation of the formula(III) compound, is reacted with an amine having the formula: ##STR14##wherein R₂ and R₃ have the same meanings as defined above, to form theformula (I) compound wherein X is S. The last-mentioned compound isoxidized by an inorganic peroxide such as sodium meta-periodate orhydrogen peroxide, or by an organic peroxide such as m-chloroperbenzoicacid, perbenzoic acid or peracetic acid, to form the formula (I)compound wherein X is SO or SO₂.

The formula (I) compounds have properties which make them suitable forincorporation in cosmetic and detergent compositions such as creams,lotions, shampoos and rinses, and the formula (I) compounds exhibitantimicrobial preservative activity therein.

The aforementioned compounds 1, 2 and 3 cannot directly constitute thebase or vehicle for pasty, creamy or liquid cosmetics and sundries, butin compositions containing other long-chain aliphatic compounds as theprincipal base or vehicle ingredients, the compounds 1, 2 and 3 havegood compatibility due to their aliphaticity, and they exhibitbactericide, fungicide, and antiseptic activity. Similarly, thecompounds 4, 5 and 6 are compatible with hydrocarbon compounds and havean excellent antimicrobial activity.

The compounds 7, 8 and 9 have physical properties similar to those ofpalm oil fatty acid diethanolamide or lauric acid diethanolamide, whichare recommended as ingredients of high-quality liquid detergents,shampoos, rinses and cleansing cosmetics. Among them, compounds havingalkyl groups containing 8 to 12 carbon atoms exhibit a foaming effectand a viscosity improving effect similar to those of lauric aciddiethanolamide, as well as a detergent effect and a dispersing effect.Furthermore the adduct of 8 to 10 moles of ethylene oxide has asurfactant activity, like that of a non-ionic surfactant, and isexcellent in wettability and dispersibility, thus being effective as adispersion base for cosmetics and sundries.

The compounds 10, 11 and 12 have a cleaning power, dispersion power andwetting power as effective as those of sodium N-alkanoyl taurate andsodium N-methyl-N-alkanoyl taurate, which are anionic surfactants.Accordingly, they are most suitable as the base having antimicrobialactivity for the anionic formulations such as shampoos and liquiddetergents.

The compounds 13, 14 and 15 have properties similar to those ofN-alkanoyl-β-alanine, a surfactant of the amphoteric type, and aresuitable for use in shaving creams, for example, to enhance synergicallythe foamability and viscosity.

As described hereinbefore, because the formula (I) compounds haveantimicrobial activity and various physico-chemical properties that makethem effective for use as the base or an ingredient of a cosmetic ordetergent base, they are usable as a base having microbial activity andthey have excellent characteristics that have not been found in theconventional antimicrobial agents.

The mixing proportion of the formula (I) compound in the composition inwhich it is used varies widely depending on the purpose to be served andwhether it is to be used for its antimicrobial preservative orantiseptic activity alone, or for its combined effect as a cosmetic ordetergent base and as an antimicrobial agent.

In the first case wherein only antimicrobial activity of the compoundaccording to the invention is desired, it is preferred to use 0.05 to 5wt.% of the formula (I) compound wherein R₁ is alkyl or alkenylcontaining 1 to 8 carbon atoms, preferably 2 to 8 carbon atoms, mostpreferably 4 to 8 carbon atoms.

On the other hand, when it is desired to obtain the dual activity as thebase or a base ingredient for the composition and its antimicrobialeffect, it is preferred to use 1 to 25 wt.% of the formula (I) compoundwherein R₁ is alkyl or alkenyl containing 6 to 20 carbon atoms,preferably 6 to 18 carbon atoms, most preferably 8 to 16 carbon atoms.Thus, the quantity to be used of the compound according to the presentinvention varies depending on the properties of the composition in whichit is used, its activity as the base component and its antimicrobialeffect. The quantity may be selected according to these criteria.

According to this invention, the compound of the formula (I) may beincorporated into compositions as shown below.

A liquid detergent composition consists essentially of 10 to 50% byweight, preferably 15 to 30%, of one or more surfactants selected fromanionic surfactants, nonionic surfactants and zwitter-ionic surfactants,1 to 15% by weight, preferably 3 to 10%, of a stabilizer and the balanceof water. As the anionic surfactants, there may be used alkali metalsalts and alkanol amine salts, for example alkylbenzenesulfonate havingalkyl group of 10 to 16 carbon atoms, alkanesulfonate having 10 to 20carbon atoms, alkyl sulfate having 10 to 20 carbon atoms andpolyoxyethylenealkylethersulfate having alkyl of 10 to 20 carbon atomsand 1 to 20 ethylene oxide units. As the nonionic surfactants, there maybe used polyoxyethylenealkylether having alkyl of 10 to 20 carbon atomsand 5 to 20 ethyleneoxide units, polyoxyethylenealkylphenylether havingalkyl of 8 to 12 carbon atoms and 5 to 20 ethylene oxide units and fattyacid alkylolamide derived from a fatty acid of 10 to 20 carbon atoms. Asthe zwitter-ionic surfactants, there may be used betain, sulfobetain, animidazol-type surfactant having a long chain alkyl group of 10 to 20carbon atoms. As the stabilizer, there may be used for example loweralcohols of 1 to 4 carbon atoms such as ethanol and propanol and glycolssuch as ethyleneglycol and propyleneglycol, urea and aromatic sulfonatessuch as toluene sulfonate and xylene sulfonate.

An oil-in-water emulsion cutting oil composition consists essentially of85 to 95% by weight of liquid paraffin and 5 to 15% by weight of one ormore organic surfaetants selected from anionic surfactants and nonionicsurfactants as defined above.

A cosmetic composition consists essentially of 10 to 70% by weight,preferably 15 to 50%, of oil or fat component selected from liquidparaffin and vegerable oil such as olive oil, castor oil, lanolinalcohol, lanolin ester and fatty acid ester, 3 to 40% by weight,preferably 10 to 30%, of one or more organic surfactants selected fromanionic surfactants such as fatty acid salts (soap), alkylsulfate of 10to 20 carbon atoms, and polyoxyethylenealkylethersulfate having alkyl of10 to 20 carbon atoms and 1 to 10 ethylene oxide units and nonionicsurfactants such as polyoxyethylenealkylether having alkyl of 10 to 20carbon atoms and 1 to 10 ethyleneoxide units, fatty acid monoglycerideand sorbitol fatty acid ester, and 10 to 50% by weight, preferably 15 to40%, of water.

A shampoo composition consists essentially of 5 to 35% by weight,preferably 8 to 20%, of anionic organic surfactants selected from alkylmetal salts and alkanolamine salts of alkylbenzene sulfonate havingalkyl of 10 to 16 carbon atoms, those of alkyl sulfate having alkyl of10 to 20 carbon atoms, those of alkanesulfonate of 10 to 20 carbonatoms, those of alpha-olefinesulfonate of 10 to 20 carbon atoms andthose of polyoxyethylenealkylethersulfate having alkyl of 10 to 20carbon atoms and 1 to 10 ethyleneoxide units, optionally containingnonionic surfactant, zwitter-ionic surfactant, oil and fat component,stabilizer and chelating agent.

The antimicrobial effect of the compound according to this invention isgenerally greater in order of --S--, --SO₂ -- and --SO-- as X of theformula I, however the effect, particularly to mold fungi, is greater inorder of --SO--, --SO₂ -- and --S--.

The present invention will be further described by reference to thefollowing illustrative examples.

EXAMPLE 1

The effect of the sulfenyl, sulfinyl and sulfonyl groups of the formula(I) compounds on the effect for inhibiting growth of gram-positivebacteria.

Following the test procedure described below with agar substratescontaining the compounds, we determined the concentration of thecompounds necessary to inhibit the growth of various micro-organisms.

According to the test procedure, 1 ml of a solution of the compound ofpredetermined concentration is placed in a Petri dish and there is added19 ml of molten common agar substrate, the mixture is agitated to makesame uniform and then is cooled to harden the substrate. A platinum loopof bacteria liquor containing a million bacterial cells per milliliteris applied to the surface of the substrate and is cultured for 72 hoursin a constant temperature room at 30° C. The minimum concentration ofthe compound in the substrate effective for inhibiting the growth isdetermined by examining the growth of the organism.

In the following tables, the indicia therein signify the following:

+: Microorganisms grow well. No effect of inhibiting the growth thereofis observed.

±: Microorganisms grow moderately. A moderate effect of inhibitinggrowth is observed.

-: Growth is stopped. The effect for inhibiting the growth issatisfactory.

The obtained results are shown in Table I.

                                      Table 1                                     __________________________________________________________________________                         Minimum concentration for inhibiting the growth                               (p.p.m.)                                                                      Staphylococcus aureus                                                                     Bacillus subtilis                              Compound           1000                                                                              500 100 1000                                                                              500 100                                  __________________________________________________________________________    n-C.sub.4 H.sub.9SCHCHCON (CH.sub.2 CH.sub.2 OH).sub.2                                             -   ±                                                                              +   -   +   +                                     ##STR15##           -   -   -   -   -   ±                                  ##STR16##           -   -   +   -   -   +                                    n-C.sub.7 H.sub.15 CON (CH.sub.2 CH.sub.2 OH).sub.2 (reference)                                    -   +   +   -   +   +                                     ##STR17##           -   -   +   -   ±                                                                              +                                    __________________________________________________________________________

EXAMPLE 2

The effective of the chain length of R₁ on inhibiting the growth of theorganisms.

The results obtained by tests similar to those of Example 1 are shown inTable 2.

                                      Table 2                                     __________________________________________________________________________                              Minimum concentration for inhibiting the growth                               (p.p.m.)                                            __________________________________________________________________________                              Staphylococcus                                                                           Bacillus     Escherichia                                           aureus     subtilis     coli                          Compound                1000                                                                              500 100 1000                                                                              500 100 1000                                                                              500 100                 __________________________________________________________________________     ##STR18##                -   -   -   -   -   -   -   ±                                                                              +                    ##STR19##                -   -   -   -   -   ±                                                                              -   +   +                    ##STR20##                -   -   -   -   -   +   -   +   +                    ##STR21##                -   -   -   -   +   +   ±                                                                              +   +                    ##STR22##                -   -   -   -   -   -   -   +   +                    ##STR23##                -   -   +   -   -   +   +   +   +                    ##STR24##                -   +   +   -   +   +   +   +   +                   n-C.sub.11 H.sub.23 CON(CH.sub.2 CH.sub.2 OH).sub.2 (reference)                                         -   +   +   -   ±                                                                              +   +   +   +                    ##STR25##                -   +   +   -   +   +   ±                                                                              +   +                    ##STR26##                -   -   +   -   ±                                                                              +   -   ±                                                                              +                   __________________________________________________________________________                                         Proteus      Pseudomonas                                                      vulgaris     aeruginosa                              Compound                 1000 500 100 1000                                                                              500 100                 __________________________________________________________________________                 ##STR27##               -    -   +   -   +   +                                ##STR28##               -    +   +   +   +   +                                ##STR29##               ± +   +   +   +   +                                ##STR30##               +    +   +   +   +   +                                ##STR31##               -    +   +   ±                                                                              +   +                                ##STR32##               +    +   +   +   +   +                                ##STR33##               +    +   +   +   +   +                               n-C.sub.11 H.sub.23 CON(CH.sub.2 CH.sub.2 OH).sub.2                           (reference)              +    +   +   +   +   +                                ##STR34##               ± +   +   +   +   +                                ##STR35##               -    -   +   ±                                                                              +   +                   __________________________________________________________________________

EXAMPLE 3

Effect of inhibiting the growth of microorganism.

The results obtained by tests similar to those of Example 1 are shown inTable 3.

                                      Table 3                                     __________________________________________________________________________                               Minimum concentration for inhibiting the                                      growth (p.p.m)                                     __________________________________________________________________________                               Staphyloccus                                                                              Bacillus    Escherichia                                           aureus      subtilis    coli                       Compound                   1000                                                                              500 100 1000                                                                              500 100 1000                                                                              500 100                __________________________________________________________________________    n-C.sub.4 H.sub.9SCHCHCONH.sub.2                                                                         -   -   +   -   ±                                                                              +   ±                                                                              +   +                   ##STR36##                 -   -   -   -   -   -   -   ±                                                                              +                   ##STR37##                 -   -   +   -   -   +   -   +   +                   ##STR38##                 -   -   -   -   -   -   -   +   +                   ##STR39##                 -   -   -   -   -   -   -   ±                                                                              +                   ##STR40##                 -   -   -   -   -   +   -   +   +                   ##STR41##                 -   -   +   -   -   +   +   +   +                   ##STR42##                 -   -   -   -   -   +   ±                                                                              +   +                  n-C.sub.11 H.sub.23 CON(CH.sub.2 CH.sub.2 OH).sub.2 (reference)                                          -   +   +   -   ±                                                                              +   +   +   +                   ##STR43##                 -   +   +   -   +   +   ±                                                                              +   +                   ##STR44##                 -   -   +   -   ±                                                                              +   -   ±                                                                              +                  __________________________________________________________________________                                           Proteus     Pseudomonas                                                       vulgaris    aeruginosa                             Compound                   1000                                                                              500 100 1000                                                                              500 100                __________________________________________________________________________                n-C.sub.4 H.sub.9SCHCHCONH.sub.2                                                                         ±                                                                              +   +   +   +   +                               ##STR45##                 -   ±                                                                              +   -   +   +                               ##STR46##                 -   +   +   ±                                                                              +   +                               ##STR47##                 -   -   ±                                                                              -   +   +                               ##STR48##                 -   -   +   -   +   +                               ##STR49##                 ±                                                                              +   +   +   +   +                               ##STR50##                 +   +   +   +   +   +                               ##STR51##                 +   +   +   +   +   +                              n-C.sub.11 H.sub.23 CON(CH.sub.2 CH.sub.2 OH).sub.2                           (reference)                +   +   +   +   +   +                               ##STR52##                 ±                                                                              +   +   +   +   +                               ##STR53##                 -   -   +   ±                                                                              +   +                  __________________________________________________________________________

EXAMPLE 4

    ______________________________________                                        Sodium polyoxyethylene (3) lauryl-ether sulfate                                                           1.2%                                              Polyoxyethylene (15) lauryl-ether                                                                         3%                                                Urea                        4%                                                EDTA                        0.4%                                              Water                       q.s.                                              ______________________________________                                    

A light-duty liquid detergent was prepared by mixing the above-listedcomponents. To this detergent there was added lauric diethanolamide(reference) as a stabilizer or a formula (I) compound of the presentinvention. The detergent was tested for the properties of light-dutyliquid detergent and the antiseptic effect. The obtained results areshown in Table 4.

                                      Table 4                                     __________________________________________________________________________                                             Properies                                                                                       Spec-                                                                         ific                                                                          Sur-                                      Concen-                                                                            Antiseptic effect                                                                          Transparency                                                                            Foam-                                                                             Perme-                                                                            face                                      tration                                                                            Test period  -3° C.                                                                     amb. temp.                                                                          ing ating                                                                             ten-                 Compound             (%)  1 day                                                                             15 days                                                                           30 days                                                                            2 days                                                                            10 days                                                                             power                                                                             power                                                                             sion               __________________________________________________________________________    n-C.sub.8 H.sub.17SCHCHCON(CH.sub.2 CH.sub.2 OH).sub.2                                               3.5  +   ±                                                                              -    trans-                                                                            trans-                                                                              211cm                                                                             8.6sec                                                                            0.49                                                        parent                                                                            parent                            ##STR54##             3.5  ±                                                                              -   -    trans- parent                                                                     trans- parent                                                                       208cm                                                                             8.5sec                                                                            0.47                ##STR55##             3.5  +   -   -    semi- trans- parent                                                               trans-  parent                                                                      202cm                                                                             8.2sec                                                                            0.48               n-C.sub.11 H.sub.23 CON(CH.sub.2 CH.sub.2 OH).sub.2 (reference)                                      3.5  +   +   +    trans- parent                                                                     trans- parent                                                                       210cm                                                                             8.5sec                                                                            0.48               n-C.sub.11 H.sub.23 CON(CH.sub.2 CH.sub.2 OH).sub.2 (reference)                                      3.5                                                     ##STR56##             + 1.0                                                                              +   +   +    trans- parent                                                                     trans- parent                                                                       205cm                                                                             8.7sec                                                                            0.47               n-C.sub.11 H.sub.23 CON(CH.sub.2 CH.sub.2 OH).sub.2 (reference)                                      3.5                                                     ##STR57##             + 1.0                                                                              +   +   +    trans- parent                                                                     trans- parent                                                                       213cm                                                                             8.6sec                                                                            0.48               __________________________________________________________________________

EXAMPLE 5

    ______________________________________                                        Sodium dodecyl-benzenesulfonate                                                                         8%                                                  Beef tallow-fatty acid sodium salt                                                                      2%                                                  Liquid paraffin           90%                                                 ______________________________________                                    

To an emulsion-type cutting oil, prepared by emulsifying the abovecomposition in 20 times its weight of tap water, there is added thecompound of the present invention, or sodium salicylate (reference), orethyl-p-hydroxybenzoate (reference). The mixture was agitated toemulsify it. These mixtures are inoculated with a mixed microbialemulsion containing a microbe concentration of 10⁶ cells/ml, of threestrains of Pseudomonas aeruginosa IFO 3898, 3919, 3924 and one strain ofEscherichia Coli IFO 3806. The compositions then are cultured withagitation at a constant temperature of 30° C. The numbers of microbes/mlof the sample after 30 days are determined by the mixing/dilution testmethod to evaluate the antiseptic effect. The obtained results are shownin Table 5.

                                      Table 5                                     __________________________________________________________________________                            Concen-                                                                           Immediately                                                                          Antiseptic effect                                                  tration                                                                           after inoc-                                                                          Test period                                  Compound              (%) ulation                                                                              after 4 days                                                                         after 8 days                                                                         after 30                     __________________________________________________________________________                                                     days                          ##STR58##              0.5  78 × 10.sup.3                                                                  8 × 10.sup.3                                                                   0 × 10.sup.3                                                                   0 × 10.sup.3           ##STR59##              0.5  53 × 10.sup.3                                                                  12 × 10.sup.3                                                                  0 × 10.sup.3                                                                   0 × 10.sup.3           ##STR60##              0.5  69 × 10.sup.3                                                                  3 × 10.sup.3                                                                   0 × 10.sup.3                                                                   0 × 10.sup.3           ##STR61##              0.5 235 × 10.sup.3                                                                 162 × 10.sup.3                                                                  64 × 10.sup.3                                                                  25 × 10.sup.3          ##STR62##              0.5 220 × 10.sup.3                                                                 112 × 10.sup.3                                                                  51 × 10.sup.3                                                                  17 × 10.sup.3          ##STR63##              1.0 938 × 10.sup.3                                                                 807 × 10.sup.3                                                                 651 × 10.sup.3                                                                 712 × 10.sup.3          ##STR64##              1.0 851 × 10.sup.3                                                                 722 × 10.sup.3                                                                 504 × 10.sup.3                                                                 628 × 10.sup.3         __________________________________________________________________________

EXAMPLE 6

An emulsion is prepared from 20% of liquid paraffin, 5% ofpolyoxyethylene (5) laurylether, 15% of the compound of the presentinvention, or sodium laurylsulphate, and the balance is water.Microorganisms obtained from the dust from the floor, wall and airinside a cosmetics plant and a detergent plant and from dirty water arecultured three days at 30° C. to prepare a microbial liquor for theexperiment. One hundred ml of said emulsion composition are inoculatedwith 1 ml of said microbial liquor, and after 30 days' cultivation, aplatinum loopful sample taken from the cultivation is inoculated in abouillon substrate and cultured 72 hours at 30° C. The cultured liquoris evaluated with a turbidimeter to determine the antiseptic effect. Onthe other hand, the emulsification power of the composition isdetermined by placing the emulsion composition in a Ukena tube, shakingit for 30 mintues and then allowing it to stand still for 24 hours. Theseparated volume is observed. The obtained results are shown in Table 6.

                                      Table 6                                     __________________________________________________________________________                            Antiseptic effect                                                             Test period                                                                   Immediately                                                                   after  After                                                                             After                                                                             After                                                                             Emulsion                           Compound                inoculation                                                                          4 days                                                                            8 days                                                                            30 days                                                                           Condition                          __________________________________________________________________________     ##STR65##              +      -   -   -   Same emulsified condition as                                                  at the start                        ##STR66##              +      -   -   -   Less stable emulsified                                                        condition than the starting                                                   emulsion                            ##STR67##              +      -   -   -   Lower emulsification de- gree                                                 and far less stable condition                                                 than the starting composition      Sodium laurylsulfate                         --                               __________________________________________________________________________

EXAMPLE 7

A shampoo was prepared from the following ingredients:

    ______________________________________                                        Polyoxyethylene laurylether                                                                         15%                                                     Sodium sulfate        0.5%                                                    Cetyl alcohol         5.0%                                                    Color and perfume     Small amounts                                           Water                 q.s.                                                    ______________________________________                                    

To samples of the shampoo there were added various formula (I) compoundsof lauric acid diethanolamide (reference compound). The antisepticeffect and the physicochemical properties of the compositions wereexamined. In these examinations, the antiseptic effect was evaluatedsimilarly to Example 6, while the physicochemical properties ofretention of viscosity, foaming behavior and foam stability, andlong-term stability were measured. The determined values are expressedas percentages based on those obtained for the reference shampoo beingtaken as 100%.

The obtained results are shown in Table 7.

                                      Table 7                                     __________________________________________________________________________                                 Antiseptic effect                                                                            Properties of Shampoo                                     Con- Test Period         Foam Stability                                       centra-                                                                            After                                                                              After                                                                              After                                                                              Visco-                                                                             stabil-                                                                            in long                 Compound                tion (%)                                                                           7 days                                                                             15 days                                                                            30 days                                                                            sity ity  period                  __________________________________________________________________________    n-C.sub.4 H.sub.9SCHCHCON(CH.sub.2 CH.sub.2 OH).sub.2                                                 5.0  -    -    -    70   65   100                      ##STR68##              5.0  -    -    -    65   60   100                      ##STR69##              5.0  -    -    -    55   60   100                     n-C.sub.8 H.sub.17SCHCHCON(CH.sub.2 CH.sub.2 OH).sub.2                                                5.0  -    -    -    100  100  100                      ##STR70##              5.0  -    -    -    95   95   100                      ##STR71##              5.0  -    -    -    90   90   100                     __________________________________________________________________________

The formula (I) compounds possess antimicrobial activity against one ormore of bacteria, fungi and yeasts. They are useful in the same way asvarious known preservatives, such as lower alkyl esters of p-hydroxybenzoic acid, sodium salicylate and the like. They can be used topreserve various different perishable organic materials against attackand destruction by bacteria, fungi and yeast. Materials requiring suchpreservation are based on carbohydrates and proteins and variousindustrial and cosmetic compositions containing fats, oils, waxes andorganic surfactants. The invention is based on the discovery of theantimicrobial activity of the formula I and their compatibility withother ingredients of cosmetic, detergent and cutting oil compositions.The other ingredients of the compositions can be any conventionalingredients used in the customary amounts.

The embodiments of the invention in which an exclusive property orprivilege is claimed are defined as follows:
 1. The method forminimizing deterioration of a non-pharmaceutical composition containingorganic materials that are subject to attack and destruction bymicro-organisms, which comprises adding to and blending in saidcomposition a compound or a mixture of compounds having the formula##STR72## wherein R₁ is alkyl containing one to 8 carbon atoms oralkenyl containing up to 8 carbon atoms, and R₂ and R₃, which can be thesame or different, are alkyl containing one to 20 carbon atoms in anamount effective to prevent or retard multiplication of micro-organismsin said composition.
 2. The method according to claim 1 wherein saidcomposition comprises one or a mixture of substances subject todeterioration by micro-organisms and selected from the group consistingof carbohydrates, proteins, fats, oils, waxes and organic surfactants.3. The method according to claim 1 in which said composition is aliquid, cream or paste cosmetic composition.
 4. The method according toclaim 1 in which said composition is a liquid detergent composition. 5.The method according to claim 1 in which the amount of said compound isfrom 0.05 to 5 wt. %, based on the total weight of the composition. 6.The method according to claim 1 wherein ##STR73## is dimethylamino. 7.The method according to claim 1 in which R₁ is alkyl having from 4 to 8carbon atoms.
 8. The method according to claim 7 in which ##STR74## isdimethylamino.
 9. The method according to claim 1 in which said compoundhas the formula ##STR75##
 10. In a liquid, cream or paste cosmeticcomposition containing perishable organic materials subject to attack bymicro-organisms, and containing a preservative effective to preventgrowth of micro-organisms responsible for deterioration of thecomposition, the improvement which comprises; said preservative is acompound or a mixture of compounds having the formula ##STR76## whereinR₁ is alkyl containing one to 8 carbon atoms or alkenyl containing up to8 carbon atoms, and R₂ and R₃, which can be the same or different, arealkyl containing one to 20 carbon atoms and is present in an amounteffective to prevent or retard multiplication of micro-organisms in saidcomposition.
 11. In an oil-in-water emulsion cutting oil compositioncontaining perishable organic materials subject to attack bymicro-organisms, and containing a preservative effective to preventgrowth of micro-organisms responsible for deterioration of thecomposition, the improvement which comprises; said preservative is acompound or a mixture of compounds having the formula ##STR77## whereinR₁ is alkyl containing one to 8 carbon atoms or alkenyl containing up to8 carbon atoms, and R₂ and R₃, which can be the same or different arealkyl containing one to 20 carbon atoms and is present in an amounteffective to prevent or retard multiplication of micro-organisms in saidcomposition.
 12. In a liquid detergent composition consistingessentially of an aqueous solution of a synthetic organic surfactantsubject to attack by micro-organisms, and containing a preservativeeffective to prevent growth of micro-organisms responsible fordeterioration of the composition, the improvement which comprises; saidpreservative is a compound or a mixture of compounds having the formula##STR78## wherein R₁ is alkyl containing one to 20 carbon atoms oralkenyl containing up to 20 carbon atoms, and R₂ and R₃, which can bethe same or different, are alkyl containing one to 20 carbon atoms, andis present in an amount effective to prevent or retard multiplication ofmicro-organisms in said composition.